Multi-step reaction with 12 steps
1: 84 percent / diisopropylethylamine, DMAP / CH2Cl2 / 48 h / Ambient temperature
2: 87 percent / NaBH4 / methanol / 0.17 h / -20 °C
3: 7 percent / (+)-2-(phenylsulfonyl)-3-phenyloxaziridine / CH2Cl2 / 1.5 h / 0 °C
4: 53 percent / (dimethylamino)pyridine, Et3N / CH2Cl2 / 0.08 h / Ambient temperature
5: 94 percent / 1,8-diazabicyclo<5.4.0>undec-7-ene (DBU) / benzene / 3 h / Ambient temperature
6: 70 percent / NaI, trifluoroacetic anhydride / acetone / 0.08 h / 0 °C
7: 1.) BH3*THF, 2.) 10percent NaOH, 30percent aq. H2O2 / 1.) THF, RT, 3 h, 2.) THF, 0.5 h
8: 94 percent / 2,6-lutidine / CH2Cl2 / a) 0 deg C, 30 min, b) RT, 2 h
9: 90 percent / DIBAL / toluene; hexane / 0.75 h / -78 °C
10: 1.) t-BuLi, 2.) HMPA / 1.) THF, pentane, a) -78 deg C, 5 min, b) from -78 deg C to 0 deg C, 1.5 h, 2.) THF, pentane, a) -78 deg C, 30 min, b) 0 deg C, 10 min
11: oxalic acid / CH2Cl2 / 1 h / Ambient temperature
12: 1.) oxalyl chloride, DMSO, 2.) Et3N / 1.) CH2Cl2, -78 deg C, 30 min, 2.) CH2Cl2, from -78 deg C to RT, 45 min
With
2,6-dimethylpyridine; N,N,N,N,N,N-hexamethylphosphoric triamide; dmap; sodium hydroxide; sodium tetrahydroborate; borane-THF; oxalyl dichloride; dihydrogen peroxide; tert.-butyl lithium; oxalic acid; diisobutylaluminium hydride; dimethyl sulfoxide; 1,8-diazabicyclo[5.4.0]undec-7-ene; (+)-2-(phenylsulfonyl)-3-phenyloxaziridine; triethylamine; N-ethyl-N,N-diisopropylamine; trifluoroacetic anhydride; sodium iodide;
In
methanol; hexane; dichloromethane; acetone; toluene; benzene;